| Physicochemical
Properties |
| formula |
C9H10ClNO2
|
C13H15NO4
|
| molecular weight
(g/mol) |
199.63 |
249.26 |
| num. heavy atoms |
13 |
18 |
| num.
atom. heavy atoms |
6 |
6 |
| fraction Csp3 |
0.22 |
0.23 |
| num. rotatable bonds |
4 |
7 |
| num. H-bond acceptors |
2 |
4 |
| num. H-bond donors |
1 |
1 |
| molar
refractivity |
52.04 |
67.29 |
| TPSA ( Å2) |
38.33 |
64.63 |
| Lipophilicity |
| log Po/w (iLOGP) |
1.62 |
2.40 |
| log Po/w (XLOGP3) |
1.65 |
1.95 |
| log Po/w (WLOGP) |
1.68 |
1.56 |
| log Po/w (MLOGP) |
1.54 |
1.34 |
| log Po/w (SILICOS-IT) |
1.90 |
1.84 |
| consensus log Po/w
|
1.68 |
1.82 |
| Water
Solubility |
| log S (ESOL) |
–2.19 |
–2.40 |
| solubility |
1.27 × 10 mg/mL; 6.39 × 10–3 mol/L |
9.96 × 10–1 mg/mL; 3.99 × 10–3 mol/L |
| class |
soluble |
soluble |
| log S (Ali) |
–2.07 |
–2.93 |
| solubility |
1.71 × 10 mg/mL; 8.54 × 10–3 mol/L |
2.92 × 10–1 mg/mL; 1.17 × 10–3 mol/L |
| class |
soluble |
soluble |
| log S (SILICOS-IT) |
–3.55 |
–3.46 |
| solubility |
5.61 × 10–2 mg/mL; 2.81 × 10–4 mol/L |
8.68 × 10–2 mg/mL; 3.48 × 10–4 mol/L |
| class |
soluble |
soluble |
| Pharmacokinetics |
| GI absorption |
high |
high |
| BBB permeant |
yes |
yes |
| P-gp substrate |
no |
no |
| CYP1A2
inhibitor |
yes |
yes |
| CYP2C19 inhibitor |
no |
no |
| CYP2C9 inhibitor |
no |
no |
| CYP2D6
inhibitor |
no |
no |
| CYP3A4 inhibitor |
no |
no |
| log Kp (skin permeation) (cm/s) |
–6.35 |
–6.44 |
| Drug-likeness |
| Lipinski |
yes; 0 violation |
yes; 0 violation |
| Ghose |
yes |
yes |
| Veber |
yes |
yes |
| Egan |
yes |
yes |
| Muegge |
no; 1 violation: MW < 200 |
yes |
| bioavailabilty score |
0.55 |
0.55 |
| Medicinal
Chemistry |
| PAINS |
0 alert |
0 alert |
| Brenk |
1 alert: alkyl halide |
1 alert: Michael acceptor-1 |
| lead-likeness |
no; 1 violation: MW < 250 |
no; 1 violation: MW < 250 |
| synthetic accessibility |
1.29 |
1.95 |
